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[ CAS No. 1001020-08-1 ] {[proInfo.proName]}

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Chemical Structure| 1001020-08-1
Chemical Structure| 1001020-08-1
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Product Details of [ 1001020-08-1 ]

CAS No. :1001020-08-1 MDL No. :MFCD11108853
Formula : C13H19N3O3S Boiling Point : -
Linear Structure Formula :- InChI Key :RITBMKDFXNCZCM-UHFFFAOYSA-N
M.W : 297.37 Pubchem ID :50873949
Synonyms :

Calculated chemistry of [ 1001020-08-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.54
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 82.0
TPSA : 126.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 0.67
Log Po/w (SILICOS-IT) : 1.57
Consensus Log Po/w : 1.46

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.915 mg/ml ; 0.00308 mol/l
Class : Soluble
Log S (Ali) : -3.71
Solubility : 0.058 mg/ml ; 0.000195 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.95
Solubility : 3.31 mg/ml ; 0.0111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.04

Safety of [ 1001020-08-1 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1001020-08-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1001020-08-1 ]

[ 1001020-08-1 ] Synthesis Path-Downstream   1~96

  • 1
  • [ 79099-07-3 ]
  • [ 107-91-5 ]
  • [ 1001020-08-1 ]
YieldReaction ConditionsOperation in experiment
100% With morpholine; sulfur; In ethanol; at 20℃; A round bottom flask fitted with a stir bar, was charged with sulfur (196 mg, 6.114 mmol) followed by morpholine (704 pL, 8.14 mmol) and the suspension was stirred at 40 C for 1 h or until sulfur dissolved in morpholine. The solution was diluted with anhydrous ethanol (EtOH), whereupon 4-N-Boc-piperidinone (1.20 g, 6.02 mmol) and cyanamide (506 mg, 6.02 mmol) were added and the reaction mixture stirred at room temperature overnight. Upon completion, the reaction mixture was concentrated in vacuo to afford viscous orange oil. The resultant product was diluted with methanol (MeOH) and then 10% ethyl acetate (EtOAc) in Hexane was added until precipitation of the product was complete. The product was filtered to afford tan solid (1.8 g, quantitative yield). 1H NMR (300 MHz, MeOH-i) d 4.35 (bs, 2H), 3.68-3.55 (m, 2H), 2.71-2.68 (m, 2H), 1.49 (s, 9H). LRMS [M+H] 298.
93% With sulfur; diethylamine; In ethanol; at 20℃; Synthesis of 2-Amino-3-carbamoyl-4,7-dihydro-5H-thieno[2,3-c]pyridine-6- carboxylic acid tert-butyl ester (3)Starting material 1 (25 g, 125 mmol) was suspended in a 250 ml bowl flask in 125 ml abs. ethanol and mixed with starting material 2 (10.5 g, 125 mmol) and sulfur (4.023 g, 125 mmol). 12.9 ml (125 mmol) diethyl amine was added dropwise to the yellow suspension, which thereby became of orange color. The reaction mixture was stirred over night at ambient temperature. Next day, the reddish solution was concentrated in vacuo and the crude product was re-crystallized in methanol. The desired product 3 was isolated as a red-brown solid (40.7 g, 116 mmol, 93%).
83% With morpholine; sulfur; In ethanol; for 8h;Reflux; Preparation of intermediate I, tert-butyl 4-oxopiperidine-1-carboxylate (30.0 mmol), 2-cyanoacetamide (30.0 mmol) and sulfur (30.0 mmol)Morpholine (30.0 mmol) was added to the absolute ethanol (200 mL) solution. The resultant was refluxed for 8 hours.The suspension was cooled to ambient temperature, and filtered through a pad of diatomaceous earth, and washed with absolute ethanol (30 mL × 3). The combined filtrate was concentrated to dryness. The crude product was diluted with 95% ethanol (30 mL) and filtered to obtain a white solid product as shown in Formula I with a yield of 83%.
82% With morpholine; sulfur; In ethanol; at 20℃; for 12h; To the stirred solution of compound 2 (6.0 g, 30.14 mmol), cyanoacetamide (3.01 g, 37.18 mmol), sulphur powder (2.13 g,30.14 mmol) in ethanol (60 mL) was added morpholine (6.01 mL,60.30 mmol) and stirred the reaction mixture at room temperaturefor 12 h the reaction mixture was concentrated, and the crude solid was filtered, washed with H2O and dried in vacuum oven for 2 h.The obtained dried compound was purified by column chromatography to yield (3.67 g, 82%) as a light yellow solid.
82% With morpholine; sulfur; In ethanol; at 20℃; for 9h; To the stirred solution of compound II (3.0 g, 15.07 mmol), 2-cyanoacetamide (1.51 g, 18.09 mmol), sulfur powder (1.06 g, 15.07 mmol) in ethanol (40 mL) was added morpholine (3.21 mL, 33.15 mmol) and stirred the reaction mixture at room temperature for 9 h. the reaction mixture was concentrated, diluted with EtOAc and washed the organic layer with H2O (2 * 30 mL). The separated organic layer was dried over anhydrous Na2SO4, evaporated and purified by column chromatography to get compound 4 (3.67 g, 82%) as an light yellow solid. ESI-MS found 298 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 11.25 (s, 2H), 7.90 (s, 2H), 4.32 (s, 2H), 3.51 (t, J = 6.8 Hz, 2H), 3.04 (t, J = 6.8 Hz, 2H).
82% With morpholine; sulfur; In ethanol; at 20℃; for 9h; To the stirred solution of Compound 5 (3.0 g, 15.07 mmol), 2-cyanoacetamide (1.51 g, 18.09 mmol), sulphur powder (1.06 g, 15.07 mmol) in Ethanol (40 mL) was added morpholine (3.21 mL, 33.15 mmol) and stirred the reaction mixture at room temperature for 9 h the reaction mixture was concentrated, diluted with EtOAc and washed the organic layer with H2O (3×40mL). The separated organic layer was dried over anhydrous Na2SO4, evaporated and purified by column chromatography to get Compound 6 (3.67 g, 82%) as a light yellow solid. ESI-MS found 298 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 11.25 (s, 2H), 7.90 (s, 2H), 4.32 (s, 2H), 3.51 (t, J=6.8Hz, 2H), 3.04 (t, J=6.8Hz, 2H).
81% With sulfur; diethylamine; In ethanol; at 20℃; Example 462-(2-(3-(trifluoromethyl)-4,516,7-tetrahvdroindazole-1-yl)acetamido -4.5.6.7-tetrahvdro thienof2,3-cipyridine-3-carboxamidea) terf-butyl 2-amino-3-carbamoyl-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylatetert-butyl 4-oxopiperidine-1-carboxylate (9.95 g, 50 mmol), cyanoacetamide (4.24 g, 50 mmol) and sulfur (1.6 g, 50 mmol) were stirred in EtOH (20 mL). Diethylamine (5 ml_, 48 mmol) was added and the reaction stirred at RT overnight. A gum had formed in the solution. Water (50 mL) was added and the solid filtered, washing with heptane (150 mL) to give a brown/yellow solid (12.0 g, 40 mmol, 81 %). MS (ESI) : m/z 298 [M + H]+.
81% With sulfur; In ethanol; diethylamine; at 20℃; for 18h; To prepare Intermediate 1, add N-Boc-4-piperidone (19.5 mmol) and elemental S (19.5 mol) to absolute ethanol (50 mL), add cyanoacetamide (19.5 mmol) to the mixture, and then slowly Add diethylamine (2.5 mL). The reactants were stirred at room temperature for 18 hours, the solvent was evaporated under reduced pressure, and the residue obtained was purified by silica gel chromatography using dichloromethane/methanol=(10:1) as the eluent for column chromatography to obtain a white solid intermediate 1. The yield was 81%.
78% With morpholine; sulfur; In ethanol;Reflux; Add tert-butyl 4-oxpiperidine-1-carboxylate (30.0mmol) in absolute ethanol (200ml),2-cyanoacetamide (30.0 mmol), sulfur (30.0 mmol), and then morpholine (30.0 mmol).After refluxing for 8 hours, the reaction solution was cooled to room temperature, filtered, washed with 30ml x 3 absolute ethanol, and the solvent was removed under reduced pressure.The crude product was crystallized from 95% ethanol (30 ml) to obtain a white solid with a yield of 78%.

  • 2
  • [ 1001020-03-6 ]
  • [ 1001020-08-1 ]
  • [ 1001020-09-2 ]
YieldReaction ConditionsOperation in experiment
53% With polymer supported carbonyldiimidazole; In dichloromethane; N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation; b) tert-butyl 3-carbamoyl-2-(2-(3-(trifluoromethyl)-4,5,6,7-tetrahydroindazole-1- yl)acetamido -4,5-dihydrothieno[2,3-c]pyridine-6(7/-/)-carboxylatete/t-butyl 2-amino-3-carbamoyl-4,5-dihydrothieno[2,3-c]pyridine-6(7/-/)-carboxylate (72 mg, 0.24 mmol) and 2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-7H-indazole-1-yl)acetic acid (60 mg, 0.24 mmol) were dissolved in DCM /DMF (3 mL/ 50 μl_) and polymer supported carbonyldiimidazole (396 mg, 1.2 mmol/g, 0.475 mmol) added. The reaction mixture was heated at 120 0C for 10 min in the microwave. The reaction mixture was filtered washing with MeOH (10 mL), EtOAc (10 mL), and MeCN (10 mL). The filtrate was concentrated in vacuo to give product as a yellow gum (67 mg, 0.0127 mmol, 53 %). MS (ESI) : m/z 528 [M + H]+.
  • 3
  • [ 1001020-08-1 ]
  • [ 104-12-1 ]
  • [ 1246966-73-3 ]
YieldReaction ConditionsOperation in experiment
57% With triethylamine; In tetrahydrofuran; at 20℃; for 8h; To a stirred solution of 4-chlorophenyl isocyanate (325 mg, 2.12 mmol) and triethylamine (444 pL, 3.18 mmol) in anhydrous tetrahydrofuran (THF) (10 mL) was added /er/-butyl 2-amino-3-carbamoyl-4,5-dihydrothieno[2,3-c]pyridine-6(7f/)- carboxylate (632 mg, 2.12 mmol) and the reaction mixture was stirred at room temperature (rt) for 8 h. The reaction mixture was concentrated in vacuo to afford oil, which was taken up dichloromethane (DCM) and washed with water (x2). The organics were then dried with anhydrous Na2S04and concentrated in vacuo. The product was purified by Isolera system (Si02gel as stationary phase, 25 g HP column, dry loading) using DCM-DCM/MeOH (0%- 8% MeOH in DCM) to afford tan solid (633 mg, 57% yield). LRMS [M+H] 451.
In pyridine; at 20℃; Synthesis of S-Carbamoyl^-β-^-chloro-phenyO-ureidoHy-dihydro-SH- thieno^.S-clpyridine-e-carboxylic acid tert-butyl ester (4)Compound 3 (1.5 g, 4.3 mmol) and p-Chlorphenylisocyanat (724 mg, 4.7 mmol) were dissolved in pyridine (12 ml) and stirred over night at room temperature. Another equivalent of isocyanate (724mg, 4.7 mmol) was added and the mixture was stirred over the weekend. The solvent was reduced under vacuum and the crude product (2.3 g, 4 mmol; light brown solid) was used in the next reaction without further purification (Content: 79% compound 4 according to UV).
  • 4
  • [ 194240-75-0 ]
  • [ 1001020-08-1 ]
  • [ 1246966-79-9 ]
YieldReaction ConditionsOperation in experiment
53% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 - 80℃; Synthesis of 3-Carbamoyl-2-[2-(4-chloro-2-fluoro-phenyl)-acetylamino]-4,7- dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester (19)Starting material 3 (1 g, 2.9 mmol) was suspended in 11 ml DMF and starting material 18 (593 mg, 3.1 mmol), dry HOBt (505 mg, 3.1 mmol) and EDCI (657 mg, 3.4 mmol) were added. The brown suspension was stirred over the weekend at ambient temperature then the reaction was heated to 80 0C over night. The solvent was reduced in the vacuum centrifuge and the crude product (a brown oil) was used without further purification (3.2 g, 22% content 19, 53% yield).
  • 5
  • [ 1001020-08-1 ]
  • [ 864927-40-2 ]
  • 6
  • [ 1001020-08-1 ]
  • [ 864927-71-9 ]
  • 7
  • [ 1001020-08-1 ]
  • [ 524693-18-3 ]
  • 8
  • [ 1001020-08-1 ]
  • [ 524691-37-0 ]
  • 9
  • [ 1001020-08-1 ]
  • [ 1585244-71-8 ]
  • 10
  • [ 1001020-08-1 ]
  • [ 1585244-73-0 ]
  • 11
  • [ 1001020-08-1 ]
  • [ 524691-53-0 ]
  • 13
  • [ 1001020-08-1 ]
  • [ 524692-54-4 ]
  • 14
  • [ 1001020-08-1 ]
  • 2-[(cyclopropylcarbonyl)amino]-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
  • 15
  • [ 1001020-08-1 ]
  • [ 1171788-07-0 ]
  • 16
  • [ 1001020-08-1 ]
  • [ 864927-41-3 ]
  • 17
  • [ 1001020-08-1 ]
  • [ 524693-92-3 ]
  • 18
  • [ 1001020-08-1 ]
  • [ 864927-95-7 ]
  • 19
  • [ 1001020-08-1 ]
  • [ 1585244-91-2 ]
  • 20
  • [ 1001020-08-1 ]
  • [ 1585244-93-4 ]
  • 21
  • [ 1001020-08-1 ]
  • [ 1585244-95-6 ]
  • 22
  • [ 1001020-08-1 ]
  • [ 1585244-97-8 ]
  • 23
  • [ 1001020-08-1 ]
  • [ 1585244-99-0 ]
  • 24
  • [ 1001020-08-1 ]
  • [ 864927-45-7 ]
  • 25
  • [ 1001020-08-1 ]
  • [ 1585245-01-7 ]
  • 26
  • [ 1001020-08-1 ]
  • [ 1585245-04-0 ]
  • 27
  • [ 1001020-08-1 ]
  • [ 1585245-06-2 ]
  • 28
  • [ 1001020-08-1 ]
  • [ 1585245-08-4 ]
  • 29
  • [ 1001020-08-1 ]
  • [ 864927-42-4 ]
  • 31
  • [ 1001020-08-1 ]
  • [ 887891-76-1 ]
  • 32
  • [ 1001020-08-1 ]
  • [ 848331-83-9 ]
  • 33
  • [ 1001020-08-1 ]
  • [ 1171063-58-3 ]
  • 34
  • [ 1001020-08-1 ]
  • [ 65-85-0 ]
  • [ 1585244-82-1 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 35
  • [ 1001020-08-1 ]
  • [ 579-75-9 ]
  • [ 1585244-83-2 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 36
  • [ 1001020-08-1 ]
  • [ 121-92-6 ]
  • [ 1585244-84-3 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 37
  • [ 1001020-08-1 ]
  • [ 99-94-5 ]
  • [ 1585244-85-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 38
  • [ 1001020-08-1 ]
  • [ 2215-77-2 ]
  • [ 1585244-86-5 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 39
  • [ 1001020-08-1 ]
  • [ 86-55-5 ]
  • [ 1585244-87-6 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 40
  • [ 1001020-08-1 ]
  • [ 1759-53-1 ]
  • [ 849660-38-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 41
  • [ 1001020-08-1 ]
  • [ 3400-45-1 ]
  • [ 1585244-88-7 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 42
  • [ 1001020-08-1 ]
  • [ 98-89-5 ]
  • [ 1585244-90-1 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 43
  • [ 1001020-08-1 ]
  • [ 64-19-7 ]
  • [ 1585244-81-0 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; General procedure: To the stirred solution of R-COOH (1.20 equiv) in CH2Cl2 wasadded EDCI (1.30 equiv), HOBt (1.30 equiv) and Et3N (2.50 equiv)allowed the reaction mixture to stir for few minutes, then added compound 4 (1.00 equiv). The reaction mixture was stirred at room temperature for 3 h. Concentrated and triturated with H2O to get solid compound. The solids were given cold ethanol, diethyl ether and hexane washings to get pure products.
  • 44
  • [ 1001020-08-1 ]
  • [ 1580443-03-3 ]
  • 45
  • [ 1001020-08-1 ]
  • [ 1580442-96-1 ]
  • 46
  • [ 1001020-08-1 ]
  • [ 1580442-98-3 ]
  • 47
  • [ 1001020-08-1 ]
  • [ 1580443-00-0 ]
  • 48
  • [ 1001020-08-1 ]
  • [ 1580443-04-4 ]
  • 49
  • [ 1001020-08-1 ]
  • [ 1580443-05-5 ]
  • 50
  • [ 39978-57-9 ]
  • [ 1001020-08-1 ]
  • [ 1580443-26-0 ]
YieldReaction ConditionsOperation in experiment
General procedure: To the stirred solution of compound IV (1.00equiv), in dichloromethane at 0C, was added DIPEA (2.50equiv) stirred for few minutes then added compound V (1.20equiv) drop wise under N2 atm at same temperature, and allowed to stir the reaction mixture at rt for 6h. the reaction mixture was diluted with DCM and washed with H2O, the separated organic layer was dried over anhy Na2SO4 and evaporated under vacuo, the obtained product was purified by column chromatography using EtOAc/Hexanes as eluent.
  • 51
  • [ 25084-14-4 ]
  • [ 1001020-08-1 ]
  • [ 1580443-27-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: To the stirred solution of compound IV (1.00equiv), in dichloromethane at 0C, was added DIPEA (2.50equiv) stirred for few minutes then added compound V (1.20equiv) drop wise under N2 atm at same temperature, and allowed to stir the reaction mixture at rt for 6h. the reaction mixture was diluted with DCM and washed with H2O, the separated organic layer was dried over anhy Na2SO4 and evaporated under vacuo, the obtained product was purified by column chromatography using EtOAc/Hexanes as eluent.
  • 52
  • [ 1001020-08-1 ]
  • 6-benzoyl-2-(4-chlorobenzamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
  • 53
  • [ 1001020-08-1 ]
  • 6-acetyl-2-(4-chlorobenzamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
  • 56
  • [ 1001020-08-1 ]
  • 6-benzyl-2-(4-phenoxybenzamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
  • 57
  • [ 1001020-08-1 ]
  • 2-(4-(benzyloxy)benzamido)-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
  • 58
  • [ 1001020-08-1 ]
  • 6-benzyl-2-(4-(benzyloxy)benzamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
  • 59
  • [ 1001020-08-1 ]
  • 2-(4-chlorobenzamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide [ No CAS ]
  • 60
  • [ 1001020-08-1 ]
  • [ 14189-18-5 ]
  • tert-butyl 3-carbamoyl-2-(4-chlorobenzamido)-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; at 120℃; for 0.333333h;Microwave irradiation; General procedure: Compound 6 (1.00 equiv) in THF was taken in a microwave vial and added NaH (1.20 equiv), respective mixed anhydride (8a-c) and subjected to microwave irradiation [Biotage initiator, temperature: 120 C] for 20 min. The reaction mixture was quenched with sat. NH4Cl and extracted into EtOAc. The organic layer was evaporated and the obtained solid product was triturated with CH2Cl2/Hexanes to get pure product.
  • 61
  • [ 1001020-08-1 ]
  • C16H14O5 [ No CAS ]
  • [ 1585244-86-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; at 120℃; for 0.333333h;Microwave irradiation; General procedure: Compound 6 (1.00 equiv) in THF was taken in a microwave vial and added NaH (1.20 equiv), respective mixed anhydride (8a-c) and subjected to microwave irradiation [Biotage initiator, temperature: 120 C] for 20 min. The reaction mixture was quenched with sat. NH4Cl and extracted into EtOAc. The organic layer was evaporated and the obtained solid product was triturated with CH2Cl2/Hexanes to get pure product.
  • 62
  • [ 1001020-08-1 ]
  • C17H16O5 [ No CAS ]
  • tert-butyl 2-(4-(benzyloxy)benzamido)-3-carbamoyl-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; at 120℃; for 0.333333h;Microwave irradiation; General procedure: Compound 6 (1.00 equiv) in THF was taken in a microwave vial and added NaH (1.20 equiv), respective mixed anhydride (8a-c) and subjected to microwave irradiation [Biotage initiator, temperature: 120 C] for 20 min. The reaction mixture was quenched with sat. NH4Cl and extracted into EtOAc. The organic layer was evaporated and the obtained solid product was triturated with CH2Cl2/Hexanes to get pure product.
  • 63
  • [ 1001020-08-1 ]
  • [ 122-01-0 ]
  • tert-butyl 3-carbamoyl-2-(4-chlorobenzamido)-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine; In dichloromethane; at 0 - 20℃; for 7h;Inert atmosphere; To the stirred solution of compound 6 (3.0 g, 10.10 mmol) in CH2Cl2 at 0 C under N2 atm, was added 4-chlorobenzoylchloride (1.42 mL, 11.11 mmol) followed Et3N (2.91 mL, 20.20 mmol) and allowed to stir at room temperature for 7 h. The reaction mixture was concentrated and dissolved in EtOAc, washed with sat. NaHCO3 (2×40 mL) and H2O (2×60 mL). The separated organic layer was concentrated under vacuum and purified by flash chromatography to get compound 9a (3.6 g, 82%) as light yellow solid.
  • 64
  • [ 1001020-08-1 ]
  • [ 329-15-7 ]
  • C21H22F3N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 8h; Preparation of intermediate II, at room temperature,To intermediate (10 mmol)To a solution of DIEA (20 mmol) in methylene chloride (60 mL) was added dropwise a corresponding solution of p-trifluoromethylbenzoyl chloride (1.1 eq) in methylene chloride (10 mL). The mixture was stirred for 8 hours and water was used,Wash with saturated aqueous sodium bicarbonate solution and brine,Then it was dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the crude product was purified by silica gel flash chromatography,Eluted with dichloromethane / methanol (5-10%),The yield of the obtained product is 63% as shown in Figure II.
  • 66
  • [ 1001020-08-1 ]
  • [ 874-60-2 ]
  • [ 1585244-85-4 ]
  • 67
  • [ 1001020-08-1 ]
  • [ 393-52-2 ]
  • C20H22FN3O4S [ No CAS ]
  • 68
  • [ 1001020-08-1 ]
  • [ 121-90-4 ]
  • [ 1585244-84-3 ]
  • 69
  • [ 1001020-08-1 ]
  • [ 98-88-4 ]
  • [ 1585244-82-1 ]
  • 70
  • [ 1001020-08-1 ]
  • [ 7154-66-7 ]
  • C20H22BrN3O4S [ No CAS ]
  • 71
  • [ 1001020-08-1 ]
  • [ 609-67-6 ]
  • C20H22IN3O4S [ No CAS ]
  • 72
  • [ 1001020-08-1 ]
  • [ 312-94-7 ]
  • C21H22F3N3O4S [ No CAS ]
  • 73
  • [ 1001020-08-1 ]
  • [ 933-88-0 ]
  • C21H25N3O4S [ No CAS ]
  • 74
  • [ 1001020-08-1 ]
  • [ 21615-34-9 ]
  • [ 1585244-83-2 ]
  • 75
  • [ 1001020-08-1 ]
  • [ 1442-03-1 ]
  • C21H25N3O4S2 [ No CAS ]
  • 76
  • [ 1001020-08-1 ]
  • [ 184951-32-4 ]
  • C18H21N5O4S [ No CAS ]
  • 77
  • [ 1001020-08-1 ]
  • [ 638-29-9 ]
  • C18H27N3O4S [ No CAS ]
  • 78
  • [ 5427-82-7 ]
  • [ 1001020-08-1 ]
  • C18H22N4O4S [ No CAS ]
  • 79
  • [ 1001020-08-1 ]
  • [ 609-65-4 ]
  • C20H22ClN3O4S [ No CAS ]
  • 80
  • [ 31301-45-8 ]
  • [ 1001020-08-1 ]
  • tert-butyl 3-carbamoyl-2-(3,5-dimethylisoxazole-4-carboxamido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 83
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 98-88-4 ]
  • tert-butyl 2-(3-benzoylthioureido)-3-carbamoyl-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% General procedure: Dissolve KSCN (117.0mg, 1.2mmol) in 10ml of acetonitrile, and add dropwise a dichloromethane solution (2ml) containing R1COCl (1.2eq) at room temperature.The reaction solution was heated to reflux for 10 min, intermediate 4 (1 mmol) was added, and the mixture was refluxed for 6 h.After the reaction, it was cooled to room temperature, filtered, and the filter cake was washed with absolute ethanol to obtain a yellow solid.
  • 84
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 874-60-2 ]
  • tert-butyl 3-carbamoyl-2-(3-(4-methylbenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 85
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 933-88-0 ]
  • tert-butyl 3-carbamoyl-2-(3-(2-methylbenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 86
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 1711-06-4 ]
  • tert-butyl 3-carbamoyl-2-(3-(3-methylbenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 87
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 938-18-1 ]
  • tert-butyl 3-carbamoyl-2-(3-(2,4,6-trimethylbenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 88
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 100-07-2 ]
  • tert-butyl 3-carbamoyl-2-(3-(4-methoxybenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 89
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 586-75-4 ]
  • tert-butyl 2-(3-(4-bromobenzoyl)thioureido)-3-carbamoyl-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 90
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 403-43-0 ]
  • tert-butyl 3-carbamoyl-2-(3-(4-fluorobenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 91
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 393-52-2 ]
  • tert-butyl 3-carbamoyl-2-(3-(2-fluorobenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 92
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 122-01-0 ]
  • tert-butyl 3-carbamoyl-2-(3-(4-chlorobenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 93
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 609-65-4 ]
  • tert-butyl 3-carbamoyl-2-(3-(2-chlorobenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 94
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 618-46-2 ]
  • tert-butyl 3-carbamoyl-2-(3-(3-chlorobenzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 95
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 2251-65-2 ]
  • tert-butyl 3-carbamoyl-2-(3-(3-(trifluoromethyl)benzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
  • 96
  • [ 1001020-08-1 ]
  • [ 333-20-0 ]
  • [ 329-15-7 ]
  • tert-butyl 3-carbamoyl-2-(3-(4-(trifluoromethyl)benzoyl)thioureido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate [ No CAS ]
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